Outland served as assistant director of boy’s work, Hale House, Boston, Massachusetts, from 1928–1930, director of boy’s work, Denison House, Boston, Mass., from 1929–1933, Neighborhood House, Los Angeles, California., from 1933 and 1934; supervisor of boys’ welfare for Federal Transient Service of Southern California in 1934 and 1935; and director of New Haven Community College in 1935 and 1936.

Outland was a delegate to the California State Democratic Conventions from 1942–1950, and was elected as a Democrat to the Seventy-eighth and Seventy-ninth Congresses (January 3, 1943–January 3, 1947). He was an unsuccessful candidate for reelection in 1946 to the Eightieth Congress. Outland was later a delegate to the Democratic National Conventions, 1944 and 1948; was chairman of the Democratic State policy committee from 1948 to 1950.